794526-34-4

Basic information

• Product Name: (3R,4S)-3-benzylthio-4-hydroxycyclohexan-1-one
• Synonyms: (3R,4S)-3-benzylthio-4-hydroxycyclohexan-1-one
• CAS NO: 794526-34-4
• Molecular Weight: 236.335
• Mol File: 794526-34-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3R,4S)-3-benzylthio-4-hydroxycyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-benzylthio-4-hydroxycyclohexan-1-one(794526-34-4)
• EPA Substance Registry System: (3R,4S)-3-benzylthio-4-hydroxycyclohexan-1-one(794526-34-4)

Safety Data

• Hazardous Substances Data: 794526-34-4(Hazardous Substances Data)

Upstream product

• 2886-59-1 1-methoxycyclohexa-1,4-diene 
• 4096-34-8 cyclohex-3-enone 
• 85808-18-0 βγ-epoxycyclohexanone 
• 30182-12-8 4-hydroxy-2-cyclohexenone 
• 100-53-8 phenylmethanethiol 
• 108-05-4 vinyl acetate 

Downstream Products

• 119478-74-9 (S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enone 
• 121652-00-4 (S)-(-)-4-hydroxy-2-cyclohexan-1-one 

Relevant articles and documents

Temporary thio-derivatization in the synthesis of (+)-4-acetylbromoxone

A stereocontrolled synthesis of the marine natural products (+)-bromoxone (1) and (+)-4-acetylbromoxone (2) is reported. The sequence features the enzymatic kinetic resolution of 4-hydroxycyclohexenone (6) via its S-benzyl adduct. Thereafter, a base-mediated elimination-silylation generated an optically active (-)-4S-4-tert-butyldimethylsilyoxycyclohexenone (5), which then underwent diastereoselective epoxidation. Saegusa-Ito oxidation enabled formation of the corresponding α,β-unsaturated ketone 13. Bromination-elimination and subsequent removal of the silicon protecting group afforded (+)-bromoxone (1) which was converted into (+)-(4S,5R,6R)-4-acetoxy-2- bromo-5,6-epoxycyclohex-2-enone (2) [(+)-4-acetylbromoxone]. Using a luciferase gene reporter assay ED50 for NFκB inhibition of 9 μM was determined.

Facile biocatalytic syntheses of optically active 4-hydroxycyclohex-2-enone and 4-benzylthiacyclopent-2-enone

Novozyme 435 (Candida antarctica Lipase B) effects the kinetic resolution of both 3-benzylthia-4-hydroxycyclopentanone and its six-membered ring analogue, providing a novel route to both enantiomers of 4-benzylthiacyclopent-2-enone and the two enantiomers of 4-hydroxycyclohex-2- enone, all in a state of very high optical purity.